


Pirate Bro

by brotherfuckers



Series: Striderclan [52]
Category: Homestuck
Genre: Anal Fingering, Anal Sex, Blow Jobs, Chains, Drunk Sex, Foursome - M/M/M/M, Group Sex, Halloween, Light Bondage, M/M, Multi, Pirates, Public Sex, Sex Toys
Language: English
Status: Completed
Published: 2013-11-01
Updated: 2013-11-01
Packaged: 2017-12-31 01:36:23
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 9,245
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1025754
Author URL: https://archiveofourown.org/users/brotherfuckers/pseuds/brotherfuckers
Summary: <blockquote class="userstuff">
              <p>Bro has always wanted to be a pirate. Always. (Well with one exception.) But his dreams are fully realized in the end.</p>
            </blockquote>





	Pirate Bro

**Age Five**

“Richard, what would you like to be for Halloween?”

“I want to be... a ninja!”

“Alright, we can find that for you. Derrick, what about you?”

“Pirate! Arrr!” Little Derrick mimicked the action of drawing a sword from his belt out and began swinging his arm around, growling at and fighting off imaginary enemies.

“Of course, we can do that too. Come on now, let’s go see what they have at the store.”

The three of them climbed into the car with Derrick continuously chatting with Richard who nodded at his brother’s gibberish and translated parts for their mother when necessary. One of Richard’s answers had Derrick in giggles when they arrived at the store. His laughter was infectious even if Mom and Richard didn’t get the joke as well. With a boy’s hand in each of her hands, they walked together into the store to find a costume. When they got to the section, she let them go and run ahead to find their costumes while she looked over the wizardly accessories. It didn’t take them long to come back with a plastic bag each. After checking to make sure they had the right sizes, the three of them went up to the front, each grabbing a bag of candy for the neighborhood.

At the checkout lanes, Derrick pulled Mom over to a specific one despite it not being the shortest line. She decided to amuse him and waited patiently. When it was their turn to checkout, Derrick pulled himself up to look over the top of the conveyor at the cashier, a young woman with voluminous brown hair and a bright smile.

“Hi there!” she greeted him.

“You’re pretty,” he told her back with an awed voice. “I’d share my treasure with you. No. I’d give you all of my treasure.”

The cashier looked bewildered, a bit flattered but confused until she caught Mom’s nod down to the pirate costume that she was holding. “Oh! Wouldn’t you rather share your treasure with your mom?”

“No. She says that Dick and I are her treasure so that’s enough for her. But I’m going to get a lot of candy this Halloween and I’ll give it to you cause you’re pretty and nice and I like your smile.”

“Oh!” Derrick beamed even brighter as a light flush crossed her face. Mom saved her by finishing up the transaction quickly but that didn’t stop Derrick from shouting “Bye!” and waving at the girl the entire distance between the register and the exit.

* * *

**Age Six**

“It’s time to plot out Halloween again. Richard, what would you like to be this year?”

“I want to be a witch!”

“Don’t you mean wizard?” Mom asked perking up.

“No, you be the wizard. I’ll be the witch!”

“‘Okay, we can do that. Derrick, how about you, sweetheart?”

“Pirate!”

“You were a pirate last year though.”

“Pirate!”

“Are you sure?”

“Pirate!”

* * *

**Age Seven**

“I want to be a knight this year!”

“Alright, Richard. Do you want to make or buy your armor?”

“Can we make it?”

“Of course. Derrick, would you like to make your costume as well?”

“Can I make a pirate’s jacket?”

“You want to be a pirate again?”

“And I can make the belt and a sword and an eye patch...”

* * *

**Age Eight**

“Mama, can we get a parrot?”

“I’m not sure that would be such a good thing with all the cats in the house.”

“Oh.” Derrick sighed dejectedly, then perks up. “Can we rent a parrot? I could keep it in my room and I promise to guard it for the week.”

“I don’t think we can rent pets... Why do you want a parrot?”

“Because every good pirate has a parrot on his shoulder!”

“And you want to be a pirate this year for Halloween?”

“Of course. Pirates are the coolest. I’m not going to be a lame monster like Dick.”

“Well I think we still have some of your old costume in the attic, we can use that and replace what you’ve outgrown. My boys are just getting so big on me.”

“Mom! Don’t kiss me. Ew! Mom slobber! Ew!”

* * *

**Age Nine**

“Mama, can I get a real sword?”

“Is something wrong with the foam one? Did it break?”

“No... just... pirates didn’t use foam swords. I want a metal one so I can plunder and pillage and take all the candy!” Derrick announced as he rested his foot on the chair seat and thrust his hand up into the air, clutching the imaginary sword.

“No.”

“Aww, please Mom? Please? Look, I’m asking nicely.”

“No.”

“Why not?”

“Because you’ll shoot your eye out.”

Derrick leveled his mother a look. “One, we aren’t in a movie. Two, I’m asking for a sword, not a gun. And three, wrong holiday.”

“It’s ironic.”

“Mom,” Derrick whined.

“When you can buy one for yourself you can get one. Otherwise, your foam sword will be fine for this Halloween.”

“You got him blood packets for his outfit,” he grumbled.

“Because he’s a vampire and going to a party. And they aren’t real blood. I just told him that.”

“Oh.”

* * *

**Age Twelve**

“I want to be Batman this year.”

Richard and Mom stopped what they were doing to turn and stare at Derrick.

“What?”

“You don’t want to be a pirate?

“No. Pirates are just so lame. They are for little kids.”

Richard and Mom traded glances.

“I’m sure we can find one still in the stores, but are you sure you don’t want to be a pirate?”

“Can we just go to the store now?” Derrick crossed his arm petulantly.

“Of course. Richard, do you need anything else to finish your costume?”

“No, I’m good. Though I can’t believe you are going with a DC hero when I am going as Wolverine from Marvel.”

“I don’t care. I want to go as Batman.”

“At this point I’m going to call you Bratman,” Richard replied snidely. There was a flash of blonde and an ‘oof’ as Derrick threw himself at Richard in a solid tackle. Mom just sighed and put the keys back on the corner, tempted to pour herself a glass of wine, but they would resolve it in about a half hour, not enough time. She poured herself some seltzer water instead and waited for the fight to stop.

* * *

**Age Fourteen**

“Can I dress Rose up as a parrot?” Derrick asked casually. “You’d want to be my parrot, wouldn’t you?” he cooed down at his little sister.

“No!” she sharply said back to him.

“Rose has spoken,” Mom chuckled at him from across the room.

“Please Rosie?”

“No!”

“Please? You’d make such a pretty princess parrot.”

“No!”

“Fine then. You won’t be the captain’s parrot.”

“No!”

“I said alright.”

“No!”

“Rose.”

“No!”

“Rosie.”

“Bo.”

“Please?”

“No!”

* * *

**Age Fifteen**

The party was actually kinda fun. For a highschool party an all. Everyone was giving his outfit a lot of compliments. Bro preened under the kind words as he really had spent a lot of time and effort to get his outfit just right (minus a real sword). There was no way he was going to have a lame costume as a freshman at a junior party.

Being D’s brother got him in the door, but the rest was him. And he’d say he was doing pretty good as he glances at the brunette and the redhead standing close to him on either side hanging off every cool word he said.

Who knew “I’d trade my treasure for your booty” would have actually worked as a pick up line?

Bro knew that D thoroughly disapproved with the look he gave when he overheard it before running off to another part of the party to get away from his embarrassing little brother but Bro was the one with a cheetah girl and Poison Ivy ready to act as his wenches.

Yeah, this party was pretty fun.

* * *

**Age Seventeen**

Bro ripped at the box as soon as he found it sitting on the kitchen table. The tape tried to fight back but yielded when he pulled out the kitchen knife. The foam peanuts fell out of the box, knocked all over the table and down to the floor as he dug under them for his prize. His fingers wrapped around the smooth surface and he pulled it out with a cry and an explosion of peanuts that had Mom rolling her eyes and D looking around the corner.

Bro couldn’t stop smiling and laughing at the replica pirate sword he held in his hand, full metal and real gems embedded in the sculpted hilt that cupped around his hand holding the leather bound grip. He slid the black sheath off to reveal the blade, not very sharp but that was something Bro could fix quick enough.

His laughs echoed all the way down from his room.

* * *

**Age Eighteen**

He could hear his brother’s eyes rolling in the back of his head when he pulled out his pirate outfit from the moving box. But like hell was he going to take the twins out trick or treating in anything less than his best. And the outfit really was getting better. Over the years he had been keeping an eye out for pieces to add like the sword and the hat. Plus he had been slowly remaking some of the pieces with better quality materials, using real leather or actual metal over sculpey clay.

The boots though... He slid them onto his feet even though it was still a week until Halloween. The soft worn leather wrapped around his feet and felt like home. They hugged his calf and playfully flopped just below the knee. Bro sighs. They were perfect.

“Take them off. It’s not Halloween yet.”

“Spoilsport.”

“Do I really look like I care, Bro?”

Bro rolled his eyes but carefully hung up the outfit and tucked the boots underneath.

* * *

The boys were off the wall excited. Their first Halloween in the new apartment complex. Bro and D didn’t know how the neighbors were going to react, but the complex had a couple other kids. And there was a small party in the lobby. Bro made sure their outfits were on right, glad for the numbers on their stomachs because D had styled their now blue hair identically to each other. Dave was Thing 1 and Dirk was Thing 2. They had played rock, paper, scissors for fifteen minutes straight to decide with a simple two out of three win rule. Freaky twin thing.

Bro was also dressed as he would accompany them through the halls while D stayed behind to pass out candy. D gave him a critical eye but actually grudgingly admitted Bro’s outfit was looking pretty professional.

With everyone ready, they headed out. Bro was systematic in the way they covered the building. At the beginning of each floor he’d draw his swords, point it down the hall, and call out, “Time to plunder for their booty!” and the boys would run hurriedly to the closest door.

* * *

When the kids finally collapsed from their sugar high back at the apartment, Bro slipped out of the door while D wasn’t looking to go after the Halloween block party that he had heard about at one of his latest gigs.

And look at that, his outfit was a hit. He had women and some men hanging off of him as he spouted cheesy pirate line after cheesy pirate line. After many attempts of pressing a solo cup in his hand despite the large black X on the back, he was finally convinced to take a cup of rum and coke under the pretense that every good pirate has to drink their grog.

He took the stereotypical Captain’s pose and chugged back the drink with just enough finesse to cover the reaction to the burn at the back of his throat that made him doubt the existence of any coke in the drink. The crowd cheered him on for the drink and then again as he started dancing to the catchy song in the background, eventually ending up on the table top.

* * *

It was maybe four in the morning, probably closer to five when Bro quietly slipped in the front door, making sure the lock doesn’t make a sound as he closes it behind him. The wide grin on his face wasn’t at all diminished by the sudden light as D turned it on from his seat on the futon.

“And where the hell were you?”

“Out,” Bro giggles.

“Out where?”

“Out’s a big place.” He stripped off the costume, tossing it to the desk where it would be repaired in the morning from where his ‘fans’ had tugged at the pieces. “Havin’ fun. Haven’t you heard of the word?”

“It’s late.”

“Course it is. Best party I’ve been to. Houston’s got the scene. Should come out with me next time.” He flopped face first down on his side of the futon. D just rubbed his eyes and turned out the light, deciding the argument could be saved for the morning.

* * *

“Plunder booty!”

“Pirate booty!”

“Booty!”

“Booty!”

The kids were already ten pieces into their sugar high that started with lucky charms for breakfast. D rued his past self from thirty minutes ago, but his past self also hadn’t had his coffee yet.

Bro was still sprawled out across the futon, drooling on the pillow. D couldn’t yet tell if he was hungover or just partied out. If he was hungover, then they were going to have some words. If he was just exhausted, well, a Strider never lets down his guard.

“Get your ass out of bed and to the roof. I have too many reasons to beat your ass down, I don’t even know where to start.”

“Wha?” Bro blearily looked up from where his face was imprinted in the pillow when the sword knocked against his head.

“Strife. Roof. Now.”

“Bluh.” Bro rolled over and swatted at the air. “Did ya get the license of the truck that hit me?”

“Nope. No excuses. Otherwise I’m calling Mom.”

Bro perked up at that threat. “You wouldn’t.”

“Don’t test me. Five minutes, roof.” D stalked out of the front door.

Bro groaned but got up, stumbling to the bathroom. He caught the boys giggling from their mostly close bedroom door. They scampered away under his glower. He knew he only had two drinks at most for the entire night, he thought back as he stared into the rough face in the mirror, so why did he feel like shit?

He met D on the roof with ten seconds to spare and then proceeded to have the weakest fight ever as D beat him down for teaching their little brothers terrible phrases and for underage drinking and other reasons D came up with. Less than ten minutes later, Bro was laid out on the roof covered in bruises and barely able to breathe.

“I surrender,” Bro groaned as D shifted his weight over his prone brother, stepping on his chest with the tip of his sword hanging down in front of him. “Also ya might wanna get off me. I feel like I’ma hurl.”

D quickly moved away. “How much did you fucking drink?”

“Two rum and cokes. I swear. A pirate drinks rum they said. But I’m a young pirate and jesus fuck if this is what drinkin’ feels like I’m never drinkin’ again.” Bro curled up on his side.

“Pansy.” D knelt down behind his brother and rubbed a gentle hand over his back.

“Fuck off and let me die.”

* * *

**Age Twenty-One**

“Yo ho, yo ho, a pirate's life for me!” Bro sung as he swept out of the bathroom in full pirate gear, “We kindle and char and in flame and ignite. Drink up me 'earties, yo ho!” He swung the bottle of rum around by the neck, “We burn up the city, we're really a fright. Drink up me 'earties, yo ho!”

D just rolled his eyes and finished putting the last details on Dave’s knight outfit. “Way to be a role model.”

“Hey, I’m legal. I bought this all by myself.”

“You’re still going to drink that around the kids.”

“Yo brats, don’t drink before you’re twenty-one.”

“Why?” Dirk immediately asked causing D to roll his eyes further. Once Dirk got started he wouldn’t stop.

“Because that’s the legal age.”

“Why?”

“Because that’s when your brain stops growing.”

“Why?”

“Otherwise it would get too big and that’s a bad thing.”

“Why?”

“Because your head would explode.” The accompanying sound effects and gestures of Bro’s head exploding derailed Dirk with a bout of giggles which ruined his princely persona he was going for. This year it was D’s turn to take them about the apartment complex while Bro stayed home to pass out candy. And drink rum apparently.

“You are going to make yourself sick.”

“Am not. See this is actual quality stuff. Like the vodka we got the other night. That didn’t make me sick. And neither has the beer and shit. Tonight’s gonna be fine!” Bro crowed as he broke the seal and lifted the bottle to his lips.

“Great. Another bad habit.”

“Go away. Take the brats and go pillage for candy.” The said brats cheered as they grabbed their bags in one hand and one of D’s hands in the other, effectively using their combined weight to pull him to the door.

* * *

D returned with two eager kids to find the candy bowl sitting empty outside of the apartment door. He frowned at that but went inside anyways, letting the kids divvy up their spoils on the floor in front of the futon. Glancing around he didn’t immediately see Bro.

Then he heard the retching from the bathroom.

With a pained expression D walked over. “I don’t even really want to say I told you so.”

“Fuck off,” Bro cursed back at him as he wiped his mouth and sat back.

“It’s never a good idea to drink a whole bottle of anything.”

“I didn’t.”

“The dregs at the bottom of the bottle don’t count.”

“Is Bro okay?” A face peeked around D’s legs.

“No, Bro’s sick.”

“Would some chocolate make you feel better?”

“Thanks, kiddo, but-” Bro couldn’t even get the sentence out before he’s leaning forward again and gagging over the water.

“No, Dave. He’ll get his candy later. Go make sure Dirk doesn’t take all of the twizzlers.”

“Okay!”

Bro groaned as he flushed away the mess and leaned his head back against the wall. “I didn’t drink it all. Barely had any. Sitting on the kitchen counter.”

D glanced over his shoulder and sure enough the bottle is mostly full, the top of the remaining rum was just above the top of the label. “Oh shit, Bro. I got some bad news for you.”

“I’m gonna die, ain’t I?”

“No. Worse.” Bro threw a baleful, miserable eye up at him. “You are allergic to rum.”

Bro leaned forward again to dry retch as his body continued to react to the rum.

* * *

**Age Twenty-Six**

“Yo ho, yo ho-”

“Oh god not this again.”

“A pirate’s got to have his rum. And I’m a pirate captain!”

“Well, Captain, might I remind you that you happen to be allergic to rum?”

“Shut up! The captain does what he wants!” Bro started to chug the amber liquid.

“Dave, Dirk. Head on out. You guys know the rules; watch out for each other, no going inside, and get twizzlers for me.”

“Yessir!” They mock saluted and head out the door as Bro finally lowers the now half empty bottle with a gasp and a swear.

“You’re an idiot, Derrick.”

“Probably.” He took a deep breath and lifted the bottle again.

* * *

Twenty minutes later, “Oh fuck, I feel sick.”

“Really?” D asked with cold amusement. “Were you expecting anything else? Even if that hadn’t been rum, you would be sick as a dog from the sheer volume.”

“Shut up and hold my-” Bro shoved the hat in D’s direction and clamped his hand over his mouth as he raced to the bathroom again.

“Try not to get any on your outfit!” D called out after him. “It’s almost complete. You’re like eighty percent pirate this year!”

“Fucking hell you assho-”

“What was that? I can’t hear you over your bad decisions.”

“I hate myself. I hate you t-”

“Yeah, yeah. I have some ginger ale for you when you are done turning your guts inside out.” D went to make the glass, getting some wet paper towels to help clean him up. “No more rum ever for you.”

“Ok-”

* * *

**Age Thirty[-Four]**

Rattle, rattle. The soft sound of chains stirred them awake. They blink blearily and take in their familiar surroundings. The living room doesn’t seem changed except for the fact that none of the brothers had fallen asleep there. Dirk and Dave are lying on either side of D. All three pairs of hands are manacled together across the top of the futon. And those leather cuffs seem to be the only thing they are wearing.

“What the bloody hell?”

“Thank you for voicing what we were all thinking, D.”

“I wasn’t,” Dave counter. “I’m kinda looking forward to whatever he has planned. This is pretty elaborate and apparently involves all of us.”

“Suck up.” Dirk kicks D who kicks Dave in proxy. “Also, how did you even get here, D? Weren’t you supposed to be at some Hollywood scary movie premiere this All Hallow’s Eve?”

“I don’t know but I have a feeling he bribed my staff.”

“Is that allowed?”

“Not at all.” D tugs on the cuffs but that just pulls Dirk’s and Dave’s hands to the center. He squirms, trying to rotate his wrists around to uncuff himself because he has a feeling about what is coming soon. Bro hasn’t missed a year since he was twelve. But D had hoped this year would be different. He hoped that Dave and Dirk dressing up as sexy nurses would keep him busy enough. D hopes that Bro isn’t going to walk in dressed like a fucking pira-

“Arg! Ahoy, ye mateys!”

“Fuck,” Dirk and D echo each other.

“Wow,” Dave sighs as he takes in his older brother. The outfit was finally complete. Every little detail was perfect. From the gold buttons with tiny skulls and leather belts with shiny buckles, to the worn stitching giving it an seaworthy look and captain’s hat with a bright orange trailing feather. Bro has even grown in and shaped a short goatee that adds to his rugged look. The linen shirt is opened, to show of a chest marked with presumably fake tattoos, down to his waist, where tight leather pants cover his legs until they tuck into his beloved boots. The long flowing jacket is impressive thrown over his shoulders with its rich materials and gold edging.

Trinkets and decoration mark the years of collected treasure and fictional stories and hang off the aged leather strap across his chest which holds an antiqued gun that has high chances of being real with his obsession. The definitely realistic sword hangs from a belt on his other side. Baubles of shells and marbled colored glass clink and shine from where they are draped around his neck. A bright blue bandana peeks out from under his hat and holds the beaded Caribbean emblems in place next to his wicked grin.

“So,” D starts after his appraisal, “who else just popped a massive boner?”

The manacles pull and rattle sharply as Dave’s hand shoots up into the air. D glances over at Dirk who is not exactly raising his hand but whose lower body has answered anyways as he tries to cover his face. Which an impossible task with how their hands are linked together.

“Why?” he whines pitifully instead.

“It is in my job description to plunder the booty,” Bro announces with waggling eyebrows that gets rolling eyes and giggles from his captives. “So who’s first to shiver my timber?”

Both Dirk and D groan at the attempted line but Dave perks up. It doesn’t take much to convince him to enjoy Bro’s dick while tied up.

“Do me, Captain,” he offers.

“Ya wanna be my wench, Dave?” Bro steps forward, unzipping his pants and pulling his dick out.

“Yes sir!” His eyes are glued to Bro’s waist and he licks his lips.

He stands next to the futon by Dave’s shoulder. “Aye then help me get my mast up.”

The participating Striders ignore the groans of the other two as Bro pulls Dave’s open mouth onto his waking cock. Dave’s soft lips and playful tongue quickly bring blood to the area until it’s hard to get a good angle from Dave’s position on the bed.

“Oi! Parrot! I need some lube.”

There is some rustling on the desk and then an orange figure darts over to land on Bro’s shoulder with a long tube. Hal is wearing a miniature eye patch and a small bandana to go along with the rest of his outfit that seems to be a cross between being a parrot and being a pirate.

“Polly wanna see some fuckin’.”

“Seriously? You had to drag Hal into this? You monster.”

“Don’t worry, Dirk. You’ll get your chance to swab my decks soon enough.” Dirk gags as Bro breaks open the lube and shifts enough to get a hand down between Dave’s thrown apart legs without removing his cock from the sucking mouth. Bro quickly works two fingers in, curling and scissoring instead of pumping because of the reach. He’s about to add a third when Dave pulls off with a wet pop.

“Please, please just fuck me now. I want it. Rough. Hard. Fast. Please.”

When Bro’s dick jumps at his begging, Bro can’t deny him. He quickly pulls his fingers out and slides in between Dave’s legs, kneeling on the futon. With a not too gentle lift, Bro gets Dave’s legs up to his shoulders and ass lined up with his hips. Dave’s arms are stretched out above his head, pulling on the chain still connected to the others. Despite their complaints the other two look on with hungry expressions and hard dicks.

Bro meets Dave’s eyes for one last check before pressing against his tight entrance. Dave’s back arches up off the futon against the intrusion, the brief pain sending bolts of pleasure as Bro slides in fully with a single stroke. Dave doesn’t give himself much time to adjust before he rolls his hips and moans at Bro, “Please, Captain! Take me hard, please!”

Bro groans and grabs Dave’s hips in a bruising grip, then starts up a brutal pace that has Dave panting and gasping in seconds. Every time Bro pulls Dave down into a thrust his arms pull tighter against the chain, jolting him and the onlooking brothers. When Dave clenches down on an especially hard stroke Bro leans in, knocking his hat askew, and bends Dave in half to start biting and sucking angry red marks into Dave’s neck, while murmuring dirty phrases and taunts into his skin.

D’s dick twitches as he catches bits like, “you lil’ slut,” and, “legs thrown wide and wanting,” which only serve to remind D that he can’t reach down and stroke his own cock. He moans half in frustration and half in want, but is cut off by the feeling of lips on the side of his own neck and a second later Dirk’s hips and erection pressing against his thigh.

“God, they are so fucking hot, D, look at them. Dave’s probably not going to be able to walk straight for days and I hate to admit it, but Bro makes one sexy pirate.” Dirk starts to rut against D’s side as he murmurs into his ear and nips at the tender earlobe and skin of D’s neck. D whimpers in frustration, unable to get any friction on his dick without turning away from the show Dave and Bro are putting on, which he definitely doesn’t want to miss. Dirk’s filthy, hushed commentary hardly helps his dilemma as his hips uselessly hump the cold air.

Bro continues to fuck Dave until a rogue moan from D’s throat makes him look over. He catches Dirk rubbing up against his older brother. Bro reaches over to smack Dirk sharply on the thigh. “Naughty slaves will get hogtied and not be allowed to come.” Dirk looks like he’s about to open his mouth. “And I’ll slap a ring around your cock and a plug up your ass if ya complain.” Dirk’s mouth quickly closes.

Bro resumes thrusting his cock into Dave, gripping his thighs to pull him towards his hips each time. Dave throws his head back with cry after cry, a mix of praise and begging for more. His own dick is red and swollen laying against his stomach nestled between his legs. The rough fucking is exactly what he asked for. The wiry brush of Bro’s goatee against him makes the skin stretched across his collarbone sensitive as it passes across with each movement.

Dave wants to reach up and grab Bro but the chains always stop him so he just pulls against them letting the leather hold him tight. Bro feels his struggle and rewards him with a sharper snap of his hips.

“Good boy, Davie, good boy.”

“Fuck! Fuck! FUCK!” Dave comes untouched, his cum splashing across his chest. Bro watches as he shudders and shakes below him but doesn’t slow down, his own climax approaching rapidly. He slams down against Dave again and again listening to the mewls and feeling the way his body clenches around Bro. He loses it when those red eyes open again and look up at him with such satisfaction. He buries himself deep as he comes, getting more moans that might have been his name as he leans forward to crush a kiss against Dave’s lips.

They both pause to catch their breath. Dave whines into Bro’s mouth when he finally pulls out and sets his legs back down. Bro uses a heavy hand to pet Dave’s hair and murmurs to him, “Such a good little pet you make. Could teach these other slaves a thing or two about obedience and gratitude.”

“What do we have to be grateful for? Waking up chained together and you don’t even have enough treasure for all of us?” Dirk pointedly tilts his head towards Bro’s now flaccid dick, “What sort of pirate are you?” He continues to mutter about Bro’s inability to plunder booty properly but trails off when he sees Bro start to grin and then full on smile. “Why are you looking at me like that? Stop that. Bro...Captain? You’re freaking me out- wait, where are you going!?” Dirk looks over to Dave and D for assistance, but Dave is still in a post-orgasm haze and D is just staring at him with a raised eyebrow.

“You brought this on yourself, li’l bro.”

“What...no you don’t think he’d actua-”

“There is a 92.37% probability that he is going to fulfill his earlier threat to ‘slap a ring around your cock and a plug up your ass’ due to your complaints and your snark levels being astronomical.”

Dirk groans and thumps his head back against the cushions in time to watch Bro saunter back into view holding a very familiar vibrator in one hand and a simple cock ring in the other, all the while still smiling like a maniac down at him. He stops to loom over Dirk, who squirms and presses his legs together, as if that would really deter Bro.

“Ya gonna spread your legs and take this easy and enjoy the ride or do ya wanna be splayed and tied down?” Dirk sighs and berates himself for opening his mouth and being sarcastic earlier but grudgingly spreads his legs. “C'mon now, Dirk. A cute li'l slave like you can do better than that. Besides, don’t ya wanna put on a good show for the audience?”

Dirk shivers at the thought, realizing both D and Dave are watching him intently, then he notices Hal hovering over Bro’s shoulder with his uncovered eye lit up red. Recording. He moans and his dick twitches as he throws one leg over the armrest and then hooks his other leg over D’s closest thigh. “Yes Sir, Captain Hot Pants.”

Bro snorts at that and kneels in front of the offered ass and grabs the lube from earlier. He slicks a couple fingers up then presses one into Dirk quickly, making him hiss from the cold lube and the intrusion, but Dirk wisely keeps his mouth shut this time. Well, he doesn’t say anything but he can’t stop the moans as Bro preps him and wraps a hand around his dick while Dirk can feel the red-eyed Striders staring enraptured.

Soon enough Bro lets him go and pulls his fingers out, but quickly slicks up the toy. As Bro pushes it in, Dirk can feel the bumps and ridges open him up even further until it is fully seated and resting directly against his prostate. Dirk squirms and then whines as his moving just makes the toy cause pleasure to go sparking up his spine. And even though he knows it’s coming he still can’t stop the whimper when Bro slides the cock ring on and fastens it at the base of his cock.

“Now be good and keep that tongue in check or I won’t take that off ‘til tomorrow.” Bro’s kiss is surprisingly tender, but then the vibrator buzzes to life and Dirk jolts against him and groans into his mouth. “You can moan and scream as much as you want though,” Bro amends his previous order when he pulls back.

Dirk does just that as Bro cycles through the settings, arching off the bed with a near silent breathy scream when the remote control slides to max. But Bro takes mercy and brings it back down to a gentle buzz which still leaves him panting and squirming.

Bro glances over and notices the flushed faces watching Dirk. D’s hard dick is bouncing against his thigh each time Dirk thrashes against him. Even Dave was starting to stir again.

“I got somethin’ special planned for ya, big bro.” D’s eyes snap to Bro’s face even as he climbs off the futon. The eyes fall to his ass until he straightens his jacket over the leather pants. Bro walks over to the kitchen and starts rummaging through the fridge, grabbing a small bottle of apple juice in reward. D narrows his eyes in suspicion as Bro unearths a fresh bottle of clear rum from the cabinet above the fridge.

“Ah, Captain?” D tentatively speaks up as Bro cracks open the apple juice. “Might I remind you,” Bro gently tilts the chilled, sweet, golden liquid into Dave’s mouth, “that you are allergic to rum? Sir?” D belated throws onto the end to stay in ‘character.’

“Oh I remember.” He closes off the juice and opens the rum. He moves around to the foot of the futon and kneels. “C’mere my pretty.”

As Bro advances, D scoots back, somehow getting his knees underneath him and sitting up a bit, but with his wrists still locked down against the chain of manacles, he can’t go far. Bro takes advantage of his kneeling position, shuffling up the futon until he is knee to knee with his brother. He grabs D’s chin and tilts his head back. With a maniacal grin, he tips the rum into D’s mouth just as he did with the apple juice for Dave.  

D somehow doesn’t splutter when the rum burns down his throat. He just swallows the first, second, and third shots that Bro pours directly into his mouth.

“Gah! Br-” he’s cut off as Bro pulls him into a kiss, his tongue pushing into D’s mouth and sweeping around to taste the remnants of rum mixed with D’s natural flavor. D’s head feels light between the alcohol slamming into his system and Bro kissing him deeply. Bro’s hand is still on his jaw, pulling him close until he starts to feel a second burn from the lack of oxygen.

He’s panting and his head is spinning when Bro finally releases him. He sucks down the cool air before meeting Bro’s eyes again.

“Are you happy now, Cap? Got your rum.”

“Oh we are just gettin’ started, you li’l rum receptacle.” D tilts his head in fuzzy confusion as Bro shuffles off the futon. Bro once again goes to the cabinet above the fridge but pulls out three different bottles out.

“Fuck, fuck, no, Bro. You’re going to kill me.”

“I just wanna taste, D.”

“Fuck. At least get me off before I blackout.”

“We’ll see.” Dave flinches lightly as two of the cool bottles are leaned against him and Bro twists open the next one. D catches a glimpse of the label before the dark rum is poured into his mouth. It’s a bit more than a mouthful so when he goes to swallow it some runs down his chin. Bro watches the drip roll over his jaw and then down his neck. Just before it hits his collarbone though, Bro swoops in and laps up the trail leading back to D’s lips.

“Ah, Bro!” D’s cries are mirrored by Dirk’s as he rocks his hips upwards against the buzzing presence in his ass. As Bro leans down to switch out the bottles of rum, he drops the remote control into Dave’s hands with a mischievous smirk. He returns to D with the bottle of coconut rum now. After over-pouring the fifth ‘shot’ into D’s mouth, Bro laps up the light spillage from D’s chest and hears the motor of the vibrator erratically shift up and down, making Dirk very vocal. Bro always knew the kid had a mean streak.

“Oh god. Bro everythings going wibbly,” D sways on his knees a bit when Bro lets him go to switch out to the spiced rum, not enough to fall over, but definitely enough that Bro holds him carefully as he deliberately splashes a bit onto his chest before giving D only a sip of the last flavor. He wants a drunk brother not a sick one. He feels D shiver through the kiss as the droplets of amber reach and tickle the sensitive skin of his hips.

Bro tips D back until he is resting on his arm before licking down the rum soaked chest, “Ya taste so good D,” murmuring as he follows those playful drips as they navigate around his abs down to the vee of his hips. He breathes cool air over the wet skin briefly and glances up at the smoldering garnets looking down at him. He ignores the silent request and leans over to catch the tip of Dirk’s cock with his lips and give a teasing suck. Dave manages to time a burst of high vibration with this making Dirk scream through a dry orgasm thanks to the cock ring.

Both Bro and Dave give him a bit of reprieve and Bro refocuses on the swollen dick hanging in front of him. As D is opening his mouth to beg for Bro to touch him, Bro does so anyways, giving him a similar treatment as Dirk but able to take much more into his throat, all the way down to the base where some rum had splashed. Bro thinks he might have a new favorite taste.

Bro works his lips over the shaft and his tongue over the head. D strains to keep himself somewhat upright between the blowjob, manacles, and drunken haze clouding his mind. The five, or was it six, shots of rum where making it hard to think, though with the way Bro’s mouth feels, D isn’t sure he needs to think. He widens his kneeling stance and Bro takes the silent invitation to reach up and play with his hanging balls with the hand he isn’t using to balance himself.

Dirk looks over and realizes Bro is no longer in possession of the remote control even though he feels it slowly creep back up. “Wha? Bro? No. Fuck, Dave!”

“Ehehe,” comes the answer from the other side of a moaning D.

“Goddamn shit! I’m going t- AH!” Dave apparently flicks it to the highest setting. “Dave, Dave, oh fuck,” Dirk pants when Dave lowers it back down.

“I want to hear you beg for it. Tell me what setting you want, Dirk. Tell me how high you want that toy plugging your ass to go. Tell me how it feels.”

“Fuck y-AH!” Dirk’s body jolts. “Hah, hah, it feels incredi-ah-ble. So fucking goo-ah! That feeling where it’s ah-lmost painful but you still wa- fuck- want more. You would love it. You’d be begging for it.”

“Beg for it for me, Dirk.”

“Please, Dave, please. Fucking make me come. AH!” As Dirk shudders again without a real release, Bro scoops up the lube and applies it to his fingers. D rocks up into Bro’s mouth as those fingers slide in behind his balls and starts opening him up.

“Ah! Fuck me, Bro! Fill me, stretch me, fuck me!” D pleads.

“You weren’t so onboard this ship when I first walked in, why should I reward ya? Maybe I should stuff you with a toy like Dirky’s.”

“No. Bigger. Please, Bro. Bigger. Fuck me. Please, Captain!”

“Wow, D. Way to be hot.” Bro slides a third finger in to stretch him just as he asked for. But from how D’s hips are rocking down against his hand, he won’t need much more. “Ya really must be feelin’ that rum.”

“Derrick! Don’t screw with me! Split me open, damn it! I want- I want-” he sobs out his pleas and pulls against his chains. Well Bro’s not one to deny a desperate man and working his brother up like this is enough incentive to get him hard again.

“Call me Captain again. Beg for me to plunder your booty,” Bro commands as he scoots back a little on the futon.

“Oh fuck, please please just fucking take me. Please Captain. Fuck my ass. Plunder my ass. Just fucking fuck me!”

In a quick motion that makes D’s world spin even more than it should, Bro grabs D and flips him over. His arms cross above his head and can’t support him and Bro pulls his hips up close. D can feel the costume brush up against him but he’s more focused on the heat of Bro’s cock pushing into him with no more fanfare. He moans deeply into the futon cushions as Bro does just as he asked and spreads D’s ass wide with his thick cock.

Just like with Dave, Bro goes at it hard and fast. His hands curl around D’s hips pulling his drunken brother onto his dick each time he thrusts forward. The staccato rhythm between ass and thighs fill the apartment under the breathy moans and grunts. D throws his head back as best he can and rolls his hips against Bro.

“Oh fuck yeah, keep doin’ that. Feels so fuckin’ good. Love hearin’ ya beg like a whore, D. Such a slut when it comes to wantin’ somethin’ up your ass. And the bigger the better, right D?” His reply is a wanton moan. D can barely focus on the words because of the rum’s cloudiness, but when he does, the dirty names send sparks all the way to the tip of his cock.

Dave is now in the same predicament that D was earlier, where he can’t look away from the coupling Striders but he’s unable to do anything about the pressing boner lying against his abdomen. Nothing except slowly crank up the settings on the remote control until Dirk’s moaning is as loud as Bro’s. Still nothing compared with D’s typical volume which Bro seems determined to hear, grabbing the back of D’s hair and pulling his face up out of the muffling cushions.

D’s world is too hazy and filled with pounding pleasure to register anything except the depth and thickness of Bro’s cock filling him, splitting him open with each thrust. Bro tugs at his captive harlot’s hair to get a sharp cry as he shoves in. D’s hands dig into the futon as his body clenches down around Bro, the tightness delicious and alluring and indicative of D’s closeness. Bro isn’t surprised at that after all of the build up.

“Br-Captain! Please!” Dave’s begging breaks through to Bro who glances over. Dave’s stomach is coated with precum and his dick ready to burst. With a knowing smirk, Bro leans over just enough to wrap a hand around his younger brother and within three strokes timed with the thrusts into D, Dave is crying out in orgasm, thumb sliding against the remote and kicking it up to full speed. The shift of angle from Bro was apparently enough to set D off as well, but his screams are actually eclipsed by Dirk’s.

The vibrator is at full strength and presses directly against that spot inside him. One leg is pressed down into the futon, lifting him up, while his other leg is tucked up under him. His body is torn between grinding down to press the vibrator and thrusting his hips up in search for something, anything to give him release.

Still pumping himself into a shaking, stiff D, Bro leans now to the other side to flick open the cock ring around Dirk’s cock. Dirk arches up through his orgasm with a voiceless scream as the finale of three orgasms crashes through him, spraying cum all the way up to the underside of his chin.

It takes Bro only a couple strokes more before he joins the others in orgasmic bliss, filling his second Strider of the morning up.

Bro collapses down over D’s back, able to feel the quivering breaths being drawn in and their shared thundering heartbeat through their skins. Dave is a boneless puddle off to the side also coated with his own release. Dirk is a twitching, whimpering mess until Bro barks at Dave to turn the damn thing off before he kills his brother. Dirk sobs in relief when the machine dies. It takes Bro a couple moments of rest before he can pull himself off of D with mutual moans.

He stumbles around to the other side of the futon and fumbles only slightly with their handcuffs though they don’t at all move once freed. With a light sigh Bro massages each wrist to make sure they are alright. Then he rearranges D to a sitting position, motioning to Dave to sit next to him for support. He leaves Dirk where he is though after checking to make sure he was still alive/conscious after carefully pulling the vibrator out and setting it aside.

Bro then wanders over to the kitchen to get a round of drinks for everyone. Water and coffee for D, more apple juice for Dave, and a pair of orange juices for Dirk and himself. After doling them out he stands again and goes to a discrete white box on the counter.

“Got donuts for breakfast.”

“Wait,” Dirk raises an eyebrow at Bro, “Why do you have donuts? When did you get donuts? Did you go out like that to get donuts?”

“Course. How else would I get free donuts.”

“I love you. I take back every eye roll and snarky comment,” Dirk announces especially as Bro opens the box when he is near, releasing the delicious scent of sugar and pastry, “Please please please gimme a donut.” He opens his mouth without letting go of the glass he is carefully holding with both hands. Bro laughs at him but obediently deposits a donut in his mouth so he can bite it. He passes the box to Dave as he sits next to D.

“C’mon drunk butt, let’s get some food into ya.”

“Murr,” D nuzzles into Bro’s shoulder.

“Yeah, yeah, I’m the best pirate, I know.”

Dave gives him a sideways glance but wisely keeps quiet.

D however, “Old orange eyes.”

“What?”

“Heh, you’re pirate name. Old orange eyes.” D giggles at that. The twins just look over at their elders with wonder about D’s fate. “Heh heh. I hate you,” his disposition suddenly turns sour. “You got me drunk,” his eyes flutter shut for a second, “so you could taste rum. Brilliant. Fucker. Is it even noon yet?” He blearily looks around as if the answer is right there. “I’m going to feel like shit when I sober up.”

“Good thing I plan on keeping you tipsy for the rest of the day. Here, drink some more coffee.” D glares at the offered mug. The aroma is alluring but Bro’s words offset its draw. Not enough though as he goes ahead and takes a sip.

They use breakfast as a chance to recover and true to Bro’s word, D doesn’t feel much more sober, just slightly more awake.

“Alright, y’all need showers. Gotta have my boys pretty when I take ‘em out.”

“Out?” Dirk repeats in disbelief.

“I got a gig tonight and y’all are comin’. Got outfits for ya and everythin’.”

“Why do I suddenly want to take back everything I said to get the donut.”

“Just help the skinny fucker get to the shower.”

Bro helps the three get to their feet and herds them to the shower. Once he hears the water running, he turns and starts getting their outfits ready.

* * *

After a lot of bribing, cajoling, coercing, and begging, Bro gets the other Striders into their complementing outfits by the time they have to head out to the club to set up for his gig.

Dave is the most willing of course, especially after he sees the high gold collar Bro had crafted. He is obviously playing the pirate’s slave role. The short jacket doesn’t cover his ribs lengthwise and entertains no thoughts about closing. The red tone perfectly matches his eyes however and Dave even admits the short puffy sleeves make him look cute. The bottom of the sleeves are banded with the same gold as the collar and bracelets that jangle around his wrists. The long, slightly ballooned, striped pants give him an an exotic flavor only enhanced by the long colorful scarves wrapped loosely around his hips, highlighting once again his mostly bare torso. Bro had even made him soft slippers that conform to his feet. Dave feels every part the captured djinni Bro has dressed him up to be.

D’s outfit turns out to be a pirate of a different flavor. It is reminiscent of Sinbad rather than Captain Jack Sparrow like Bro’s outfit. The long white blouse also does nothing to cover his chest as the two sides of the neck are only held in place by the dark red ribbon wrapped around his waist before being tied off. The long loose end is prone to flutter in the wind (or whenever the air conditioning kicked on in the apartment). Loose slacks are tucked into the tops of high boots whose toes curl up at the end. The heavy gold medallion around his neck glitters as light catches on its many facets. His blonde hair is wrapped up in a turban like dressing and Bro rubs a bit of charcoal on his face to give the impression of a dark beard instead of blonde.

Dirk fights the most against his outfit, claiming it is just a ‘genderbend’ of the stupid halloween costumes you could find at Walmart. The particularly short black shorts show off his long legs with high boots (thankfully flat soled) and have orange lacing up the sides. He is a bit mollified when Bro adds a couple belts around his waist, criss crossing across his hips with sheaths for some small daggers. He realizes the recurring theme with exposing shirts as the black and white striped one falls short of covering his abs. The jagged edge stops just below his chest. The sleeves have similar orange lacing up the sides. Bro’s final bid is the hat he offers. A three point with a white feather that trails down to his shoulder blades. Next to Bro he looks like a low crew member, but without the comparison, it is a decent costume.

Bro grins wildly when he gets them all lined up.

“I love y’all.”

“You big doof.”

“You owe us bad.”

“Can I suck you off under the DJ table?” Dirk and D turn to stare at Dave.

* * *

And that’s exactly what happens at the club. Bro gets them in under the guise of being his backup dancers slash groupies. The outfits apparently give them enough cover as to not look suspiciously related. Bro is announced in as DJ Piratefreak instead of his usual title. And following that line, he plays pirate remixes that he had found and collected previously to a rocking, bouncing club that just cheers for more.

“AARRRRR YA READY!” He shouts into the crowd a breath before he drops the bass which sends all the party goers wild. At the same time, Dave deep throats his brother under the cover of the table in the DJ booth. Bro is glad the music is loud enough to hide his moan because damn Dave’s mouth feels good around his cock. With one hand on the back of Dave’s head, Bro rocks with the beat that he controls.

Dirk and D had excused themselves from that area but still blend well with the costumed crowd and now are hanging out near the back. Dirk pushes another glass of water into D’s hands.

“I wish he’d stop being so hot in public,” Dirk complains, actually a little miffed because he wouldn’t mind being involved like Dave is, especially with the crowd just on the other side of the thin wall.

“I wi- wish I weren’t so frick frack cadillac wasted. Fric- freak- fucking rum. Bloody pirates.” D sways on his feet.

“D? Do you need to lean on a wall or something?”

“Dirk? Can I take you in the back and...” D trails off distractedly. “I need you to suck my dick.”

Dirk snorts a bit into his own water and stares at his brother until D pushes his hip against Dirk’s hand to show off the boner in question. The one now growing in Dirk’s hot pants doesn’t have much room and makes the situation urgent.

“Yeah,” Dirk chokes out and basically drags D out the nearest exit.

Bro catches the flash from the long white feather and smirks at his brothers just before he gives the signal to Dave that he’s close. Dave doesn’t stop sucking and swallows Bro’s load down a couple beats later.

* * *

Hours later the Striders collapse back onto the futon, where they had started their pirate and sex filled Halloween. The twins are nearly asleep before their heads hit the pillows. D manages to lift his long enough to laugh at Bro.

“You finally got your day of being a pirate, Derrick. I guess dreams really do come true.”

“Yo ho, a pirate’s life for me.”

“No. You only get a day.”

 

**Author's Note:**

> For more information please check out our work at striderclan.tumblr.com; we have more stories, head canons, art/pictures.


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